I have not done that trip per se, but I have been in and out of Salem and in and out of Nantucket, and a fair number of places between, many times.
Short of weather, I can't think of any reason why you couldn't do this trip comfortably in a week+. I wouldn't hesitate to do it with a 3 year old that is accustomed to sailing -- and here I assume yours is -- provided you are not the lone adult that must both sail the boat and watch the child. PFD at all times while on deck for the kid, of course.
A good route would be to jump down to Scituate from Salem. Then down to the CC canal. Spend a night in or around Hyannis, then out to Nantucket the next day. Spend three or four days in Nantucket. Coming back, you could do P-town instead of Scituate.
Just a suggestion... Sounds like a great trip. Nice to do it before the windmills go in.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT